Acetic Acid → 2-(3-Bromobutyl)-3-methyl-6-nitrophenol

HRID 637627Notes

Reaction equation

HRID 637627 reaction equation
C[CH:2]([C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=1[OH:15])[CH:3]=[CH2:4].[BrH:16].[C:17](O)(=O)C>>[Br:16][CH:4]([CH3:17])[CH2:3][CH2:2][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=1[OH:15]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 202555762-(1-Methyl-2-propenyl)-3-methyl-6-nitrophenol

Product 1

HCID 135602952-(3-Bromobutyl)-3-methyl-6-nitrophenol

Conditions

Temperature
113 °C

Procedure

A mixture of 155 ml of the crude 1B, 15 ml of glacial acetic acid and 135 ml of 48% hydrobromic acid was stirred at reflux (113° C.) for five hours, then concentrated at 30 Torr. and 80° C. for one hour. The residue was taken up in 500 ml of ether, dried (MgSO4), and filtered through Celite, and the solvent was evaporated from the filtrate. The residue was column-chromatographed on silica gel, using a 1:24 v:v mixture of THF and hexane as eluent. The product was recrystallized from ether/hexane to give 2-(3-bromobutyl)-3-methyl-6-nitrophenol (1C), as a light yellow solid, m.p.: 67°-69° C.

Workup

  1. concentrationconcentrated at 30 Torr
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered through Celite
  4. customthe solvent was evaporated from the filtrate
  5. customThe residue was column-chromatographed on silica gel
  6. additionv mixture of THF and hexane as eluent
  7. customThe product was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-4a2ace7de9414a52922d20376da7ea3a
Source dataset
uspto-grants-1985_12
Patent number
US04558040

Reaction notes

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